Thirty Minute Mentors Podcast Transcript: Baseball Legend Shawn Green

I recently interviewed Shawn Green on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today was a star for the Dodgers and Blue Jays during a 15-year Major League Baseball career that included a couple of all-star game appearances, a Silver Slugger and a Gold Glove. Shawn Green is the co-founder of Greenfly, a leader in digital media monetization. Shawn, thank you for joining us.

Shawn: Yeah. Thanks, Adam, for having me.

Adam: Before you became Shawn Green, star and Major League outfielder, you were Shawn Green, high school student in Orange County, and top amateur prospect deciding between playing baseball at Stanford and turning pro and signing with the Toronto Blue Jays. You had two highly compelling opportunities. And it was a big decision point in your life at an early age. Can you take listeners back to that moment, back to that decision, and share the best lessons that you learned from it?

Shawn: Yeah, that was a challenging decision to make. At the time I was 18 years old. I was a good student and always planned on going to Stanford. And then the Blue Jays drafted me in the first round with the 16th pick in June. And back then you had until you stepped in your first class at the university to sign with the professional team. And once you do that, you're no longer, obviously, going to play in that college. And Stanford was on the court system. So, they started in September. So, the blue doesn't really talk to me much. I broke my thumb playing baseball in a summer league game and couldn't play that summer if I had signed anyway. So, I was just, kind of, going about my summer. And then as it got towards September, the Blue Jays started coming after me a little hotter and getting more aggressive with their offers. And I saw a sign. I went to Stanford and went to the first baseball practice. And the last day before class started, they came in with an offer. That was where we had told them we wanted to be and so I had to let Mark know, Mark was the head coach there, no. My dad said, “Hey, you have to go and talk to him like a man and tell them what you're going to do”. And I was scared to death. You know, this guy is a legendary college coach. And he had coached the Olympics already at this point and won two championships, in ‘88 and ‘89. And here I am, it's 1991, so a couple years after that. And so, I walked over there. And he completely talked me out of it. He flipped me. As a successful college coach, you have to be a good recruiter, a good salesman, so he was able to sell me on the concept that it was better to stay and play at Stanford. And so, I called my dad and called him crying, I know what to do. I decided, I think I'm gonna stay. And so, then my quote-unquote “advisor” who became my agent for a long time, Jeff Moorhead. He had me talk to another player there. And that was one of the things I was really worried about. I didn't want to leave them high and dry. Because that year, for the first time in a long time, Stanford had lost two other players to the draft, because now at this point, the money was starting to get more tempting. And so, they had lost Shawn Estes and another guy. Shawn Estes had a long career as a pitcher with the Giants and Mariners and a bunch of teams. And so, I talked to another player and he said, “How much did they offer you?”. And I told him how much they offered me. Every other guy on his team would take that. So, I would tell you to take the money and go. And so, at that point, I called Mark, because I was scared to go back to his office. I already went down that path and it didn't work out. So, I called him and he said, “Hey, you're gonna sign”. And he was really nice, respectful, and I ended up staying there and taking classes. But at that point, I was no longer going to be on the baseball team. And I went to the Fall-Winter quarter and off to Spring training and did that for a couple years.

Adam: I think there are a few really important lessons in there. First and foremost, seek the counsel of others. Whatever the decision is, it's hard to make a loan and you went out and you asked one of the guys on the team, what should I do here? What would you do if you're in my shoes? Regardless of where you are, it's so important to seek the input of those around you. Another important lesson is that you have to make hard decisions. There are going to be difficult decisions, no matter what phase you are in your journey. And this was a big one you had to make early on. And it clearly impacted the trajectory of your career.

Shawn: Yeah, I mean, that's a really good point. And it's something that's hard for me because I never liked to disappoint people. So, to tell someone, essentially rejecting them or their offer or their opportunity that they’re presenting you with, is a really hard thing. But whether it's having to fire someone that's not working out, you have to make those moves and do things that are right for your company or right for the path that you're trying to put forward for the people that are relying on you. And that was a really hard thing to do as an 18 year old. Letting down someone I looked up to, but again, when you have to make a decision like that, whether it's breaking up with someone, it doesn't serve anyone's interest to be in some type of relationship, working relationship, partnership, that you're not all in. And I learned that that's one of the first lessons for me in that type of outcome that I had to set for it.

Adam: Shawn, your story also brings to mind something recently that transpired with the UCLA basketball team. One of their players, Miles Johnson, had one year of eligibility left. And he announced that he was not going to return to the team even though UCLA has this great team, he would play a key role on the team. And he's not turning pro. He's not testing the NBA Draft. He's not trying to play basketball in Europe. He's instead going all-in on his academic and engineering career. He's pursuing a master's degree in engineering. And when he met with UCLA basketball coach, Mick Cronin, and asked him, “What should I do? What advice do you have for me here?”. What Mike Cronin said was, “You have many good options. And you can't go wrong with any of these options. So, regardless of what you do, you're going to be fine. They're all good choices”. And the reason why I bring this up is because not only do you ultimately have to make a decision, but by seeking the counsel of others, if you're asking the right people, if you're asking the right mentors to help you with your decision, they're not going to make the decision for you. But they're gonna help you and provide you with counsel and with wisdom and with guidance so that when you do make the decision, you feel comfortable that you've made the right decision.

Shawn: That's exactly right. Even talking to a player that was three years older than me or two years older than me on the team, he had that experience of what it would be like for me there and what the opportunity would be taking the path that he was going to take after that season when he got drafted. So, to be able to talk to people that provide more information. The old saying, “Where you can share knowledge but you can't ship them”, right? Wisdom is something you have to experience but to pass on. Okay, this is the knowledge that I extracted through my years that gave me wisdom. I'm gonna pass that knowledge on to you and then you make a decision and you've experienced those things. And over time, you'll get much wiser in that particular area or that career or whatever it is. And so, that's what I tried to do. I still try to do it. I try to get these different sides of knowledge and different aspects of information about things and just pull it all together and assimilate it and figure out what is the best path for me.

Adam: Your first two years in the minors were, what would you say, underwhelming. Especially considering that you're such a highly-touted prospect. And for listeners who are not baseball fans, I'm gonna throw some numbers out there. Your first year in the majors, you broke into the majors in September, and you had a batting average of 0.91., an on-base percentage of 118., and a slugging percentage of 121. If you are a baseball fan, you'll understand what I'm talking about. If you're not a baseball fan, even if you double those numbers, you're still in trouble. But then the next year, you come back and finish in the top five in Rookie of the Year voting. And the rest is history. You go on to have such an incredibly successful career. How did you navigate and ultimately overcome those early struggles? And what advice do you have for anyone on how to navigate and overcome whatever struggles they may be facing in their lives or in their careers?

Shawn:  Yeah, and that's the thing about being a baseball player, there's a lot of ups and downs. If you fail seven out of 10 times, you're a Hall of Famer .300 average is pretty rare - to have a career 300 average, which I didn't, I was like a 280-something hitter. But early on, those numbers, the first September I was over six up. So, those things are coming; they don't really count those more about the minor league season. The next year, I was up to 30 some odd at-bats and that's where the numbers you referenced, but did well in triple-A but really the bigger challenges came out this first few years of playing in the major leagues right one the that year that I hit 0.91. With the Blue Jays, I actually won the batting title at triple-A in the same year and the bigger number of at-bats. So, I was highly touted coming in. And then my rookie year I played only against right-handed pitchers, and that was hard for me and had a good year. And then the next year, same thing, and I started slow each year and then built up as the season went on. So, there's a lot of ups and downs and then finally my third year to two years of hitting in the 280s and clang most of the time but not all the time. Which, again, was super frustrating. I was supposed to have a chance to play every day, but got off to another slow start, didn't get that chance to play every day, and actually got benched. And that was really the low point for me and my career is when, after playing a lot and doing well, I was always done on the bench. And my manager didn't really like me in Toronto, early on, because he had just won a couple World Series. And now he has these young players that the front office was really wanting to push and get in the lineup and kind of like the veteran player. So, without giving too much backstory there, I was in the spot where I was caught between a little bit of a power struggle. And once I got back in the lineup, I decided, you know what? I have to have an approach that is consistent with who I am and what I want to be. They really wanted me to try to pull a hitter, so for the non-baseball fans, it is to try to generate more power and hit the ball to the right side as a left-handed hitter. And I was more of a guy that hit the ball to all fields. And so there, you sacrifice a little bit of the power numbers, the home runs, and all that, but on the hit for a higher average. And so, I finally just came to the realization, I'm sitting on the bench, I gotta do what I need to do. If I'm gonna fail, I'm gonna fail going with the path that I most believe in. That's the big lesson for me, it's really, whether you're an athlete, or stuck founding a company, or whatever it is, it's really on you. You have to take in information from all sources and decide, okay, this is what I believe in, and you have to trust it. And that's what I did. And that's when my career really took off. I did super well and I got back in the lineup, and the manager got fired. Then the new season manager came in and I was playing every day. And that's when things took off for me. So, that one bit of adversity specifically was a key for me, becoming a better player and trusting myself and what I believed. Had I not gone through that I probably would have had a long career that was solid, but I don't think I would have taken it to that next level because I wasn't pushed to that point where I had to just really bear down and say, who am I? And how do I want to play this game?

Adam: I love that. Adversity is integral in helping you become a better version of yourself. The importance of understanding who you are, knowing who you are, and trusting who you are. And finally, I'm going to quote Rojas. I had on this podcast the great Victor Rojas, he was the play-by-play announcer for the Angels. He didn't quite have the career on the field that you did. But when he was talking about what it takes to be successful as a broadcaster, which, in reality, is what it takes to be successful in anything. He said, “Don't try to be the second-best version of anyone else. Focus on being the best version of yourself”.

Shawn: I mean, that's exactly right. And a lot of people ask me, like, who are your best coaches? And I tell them there's certain coaches I had a great relationship with who are good cheerleaders and got me through some tough times. But I believe in talking to teammates, and guys like Carlos Delgado and Tony Fernandez. Talking to players and other teams like Dave Justice and watching them and then taking all that information and pulling it together into who I want to be. And not trying to be like them or copy other people, but grab little pieces from everywhere. And that's the same thing we do with the business GreenFly. You see other successful companies and what are they doing? How are they driving business in the sports world? Or how are they finding good talent? And you start to pull from all these different sources and you create your own identity and what it's going to take for you and your business to be successful.

Adam: You mentioned a couple of great players Carlos Delgado, David Justice. You played for a number of different teams over the course of your career, several different managers, many, many, many different teammates, even more opponents. Who are the best leaders that you played for and played with? And in your experience, what are the key characteristics of a great leader?

Shawn: It's hard to answer that as there are a lot of great players and leaders I played with. I would say the best leaders are still leading. So, Tony Fernandez, who's now the head of the Players Association. To play with him in Arizona and he’s a tremendous leader, him and the other guy that I briefly played with in Spring training. My very first Spring training in 1982 was with Dave Winfield. And both of them, when they would speak in a meeting, the whole room would be quiet. And one is they both had tremendous work ethics. So, it's not someone trying to pipe in about what needs to be done, if they're the last one to show up at the ballpark at first when they leave. But these guys work really hard. And, I think, it helps that they're both really big guys. They just had a big presence anyway, that's not crucial in any stretch, but the way they presented information and spoke. They had a very confident tone in their voice. They spoke slowly and emphatically. I think just speaking at dynamics is a big part of it. Carlos Delgado is, as I said, he was a great leader in baseball. I played with him for 10 years. And a guy who's not a big star on the team, Alex Cora, who's doing a great job with the Boston Red Sox. He was just a very knowledgeable baseball guy. And on the field, if anything was going on, he would step in, and he knew all the rules, and he was just a field rat and loved it. Absolutely loved baseball more than anyone I think I ever played with. And, I think, that love for the game has given him the respect of teammates and the players that play under him, because they know that he loves what he's doing. And he knows a lot about it.

Adam: You named a number of great players. You also named some characteristics that are essential. Communication, passion, and leading by example. Going out there and being someone who not only talks the talk, but walks the walk.

Shawn: Yeah, without a doubt. The people who sometimes yell the loudest as the team is struggling, that come on, let's go, get a lot of that stuff. It doesn't carry any water if the person isn't leading by example. I think that's the biggest thing, especially in baseball, because it's pretty hard to fool your teammates because you're there every single day. You're like brothers and play 162 games, and 181 days plus another 40 some odd days together for Spring training. So, you know each other really well. And something like a 20-game schedule or something like that. And maybe people could fake it a little bit here and there. And they're working hard. But at baseball, you see people, what they're doing each day. That is probably the biggest thing is how do you carry yourself and what are you doing? Are you working hard? And those guys that I mentioned are some of the guys that definitely worked the hardest, and also had the confidence to speak up when they needed to. 

Adam: You had a reputation as a great teammate across all the teams you played for. Now, you're running a highly successful technology company. What can anyone do in any organization, whether it's a sports team, a technology company, a nonprofit organization, any business? What can anyone do to be a great teammate? And what do you believe are the most important elements to fostering winning teams and winning cultures?

Shawn: That's, I think, the biggest thing that's helped me in my transition in the business is understanding team dynamics. There's always going to be conflicts that pop up between people internally, externally, whatever it is. And trying to understand what's going on in your personal life is everything. Okay, we're all human beings. And there's a lot of challenges in our personal lives, in our business. And to be able to perform your best, you have to be in a good headspace. So, if there's a conflict between team members, whether it's something that needs to be done on an individual basis, or collectively, to say, hey, what's going on? Like, how can we actually work through this? To just talk about it or like, hey, I understand that maybe you need to look at things a little bit differently. And just to talk through different situations. Also, it's important when you're bringing a team together to try to find people that are going to fit with the others that are part of your organization. Well, and that's something in sports a lot right now, that is sort of taking a backseat and particularly with baseball. The Moneyball things, kind of, became all about the numbers and all about the data. And having that chemistry is as important in a lot of cases as having the spin rate or exit velocity, you're on-base percentage, whatever. The general managers are focused on a specific organization, the chemistry has to take more of a front seat. You see it in teams that when they find ways to win that aren't supposed to win, they do that because they get along really well. And they have each other's backs.

Adam: Which is interesting considering that you've been able to see things through both sides of the spectrum, as a player, now as an entrepreneur. As an entrepreneur in a company that deeply understands technology, deeply understands data, but also understands people, understands the human side of business. And I want to ask you about that. What sparked your interest in entrepreneurship? And what are the best lessons you've learned from your playing days that you've been able to apply as an entrepreneur and as a business leader?

Shawn: So, I always loved tech and during Spring training I would, every year I'd buy some type of how to code or how to Final Cut Pro or Photoshop. Some of the stuff was, I never really learned it. Photoshop and Final Cut I got pretty good at but, yeah. The coding, I hit their chapter and I was just so exhausted mentally from playing baseball, they were long, but I just couldn't quite get my arms around. But I still love tech. And I was passionate about it just the same way I was passionate about baseball. Especially when I was younger and just loved it. And that's something I learned pretty quickly. We already spoke about the fact that passion is what drives success. And towards the end of my baseball career, I was losing the fun of it. And it became work. Being away from my family, traveling and all that stuff. And so, I got really excited about the tech and so, I just figured things out as I went. And fortunately, my cousin is a brilliant guy and he had recently moved out to L.A. to work at Activision Blizzard. Daniel Kirschner, he was intrigued by what I was doing. And I was looking for someone to run it. Yes, one thing I did learn is a personality trait. I always preferred to be the number two guy when I was playing and when I got traded to L.A, I had Gary Sheffield and I was kind of his wingman the first couple years. And then before that in Toronto, I was Carlos Delgado's wingman. And I like to, kind of, just be a step behind someone else. And that's just my nature. I don't want to be in the spotlight. And then when I found that Daniel was interested in joining, I wasn't going to try to talk my cousin into leaving a great job and coming to a startup with a family member. He did his research and got excited about what the opportunity was. And originally it was just going to be more of a video Q&A platform. And to give you a little bit of the history. So, our idea was to get a network of people and just build a simple video Q&A. Where broadcasters can tap into a network of people, and someone has a blown torn ACL then they can type an ACL injury and team doctors or other athletes that had that same injury could get an alert and create a video that they put on air right then. And that was the original concept. And also for fans, whoever else was relevant to telecast. And what happens, we did that for a couple of different things in college football, and then we did March Madness about seven, eight years ago. We did a deal with CBS and Turner. And we sourced like 100 people relevant to the different schools. And Ashley Judd for Kentucky was there. And Tom Arnold for Iowa, Christian Laettner. And so, tomorrow, we'll give a graded halftime pep talk for Iowa when they were losing the waiver round. It was super funny. And then they put it on air and did a lot of the stuff online. And coming out of that we got Maverick Carter, who's LeBron’s business partner and longtime friend. They were building Uninterrupted and just launched it. And they reached out to us because they had a relationship with Bleacher Report, which was Turner, and said, “Hey, we'd love to license your tech, we're building this personal content platform called Uninterrupted”. And at first, we're like, hey, that sounds repetitive. But we're kind of hesitant. And then we just realized that everyone has a network in sports, whether it's a team, it's a league, broadcast company, or brands, and they all have this network of people that's valuable to them. And for us to be the software that enables them to move content around. And so, that's when we really shifted our focus to build a software as a service product. And it's like, hey, if they want to get content from people, they probably want to get access to all their content as well. So, that's what we do now. In our biggest customer, our biggest leagues around the world and small leagues as well, where they have all their photos and short-form video content flowing through our system, it automatically gets sent to the right people. So, whether it's the players getting off the field, or the court, they have all their content. If it's a broadcast partner, they have all their content. And if it's a sponsor, they can have their content. So, all the stuff is moving automatically through our system. And that's how GreenFly became what it is today.

Adam: Such an important lesson there. Shifting your perspective, not being set in your ways, and being willing and open to thinking of your competitors as potential collaborators. In your case, it was a complete game-changer for your business.

Shawn: Yeah, that's so true. And that's both competitors and customers. And that sounds great. And by listening to what these great customers have that we have, most of the major leagues around the world have a lot of information that they could share and whatever major league baseball needs. I'm sure Gunas Liga, and UEFA, I'm sure they're gonna need very similar things. And the same thing from the competitor standpoint. And there's really nothing out there that solves the problems the way we solve them. But there's competitors who have just little aspects of what our platform does, and to see, okay, they're focused on this one thing, and they're doing it pretty well. So, maybe we should make sure our platform is tuned in that way as well. So, we can handle those problems and it's just being open and listening to what the market is telling you. And that's probably the most important thing. And it gets a lot easier the more customers you have because there's more voices to hear.

Adam: Listening is essential to success as a leader, essential to success as an entrepreneur. You’ve long been identified as not only a great baseball player, but a great Jewish baseball player. Which is notable because relatively speaking, there haven't been many Jews who have played Major League Baseball, let alone have become star Major League Baseball players. Most Jewish baseball players have the kind of baseball careers that I had, which we'll just call it unceremonious. I was the captain of the worst high school baseball team in the history of high school and probably in the history of baseball. But in your case, you were one of the best players in baseball, and you didn't grow up with a religious background. But you often found yourself as the only Jew in the clubhouse. And it made you, in some ways, a symbol, because of your religion and your heritage. How did you develop a level of comfort in your skin to embrace rather than to shy away from being different and being other? And what can anyone do to get to a place where they can feel comfortable being themselves, regardless of who they are, regardless of their surroundings?

Shawn: Yeah, it's hard to get to that place sometimes when you're young, especially. I have two teenagers. You want to fit in as a teenager, you don't really want to be different. You want to be like everybody else, right? And then you get in your 20s. And you're trying to be like people at your first jobs and trying to fit into the company culture. I didn't really talk about being Jewish. For a while it, kind of, got out there, I would say maybe a year or two into being in the big leagues. And then I was playing Toronto, which has a very nice, big Jewish population. So, it was known there. And then it didn't start to become more of a public quote-unquote, “baseball knowledge” until, I think, I started having a lot more success. And you make me the all-star team in ‘99. And all of a sudden people are like, “Oh, this Jewish kid made the all-star team”. And then everywhere I went, there'd be Jewish publications or one time Bud Sila wanted me to go speak, who was a commissioner of baseball at the time. When we go speak in Chicago to JCC in a community where there was a hate crime. So, all of a sudden, I became this Jewish figure alongside being a baseball player and all that comes with it. And there's two ways you can go: you can hide from it or you can embrace it. And I embrace it. I was always proud to be Jewish. I wasn't one to go out and try to advertise anything. But stuff gets out there. And it's like, yeah, I'm Jewish. And then all of a sudden, there's a conflict with a game and the High Holidays and Yom Kippur war, and I had to make a decision. And then I opted to sit out a game for, I think, three different seasons. And it wasn't as much of a strict religious decision as it was like, Hey, I'm a role model for a lot of kids that look up to me being one of the few Jewish athletes. And they can all-star teams and do that type of thing in any professional sports in the U.S. So, I felt like it was important to really stand for that and say, hey, I'm proud to be Jewish. I'm gonna sit down with the poor and serve the high holiday. And the first time I did that, it was 2001. So, it was literally a week or two after 9/11. So, it wasn't a story at all. Obviously, there's much more important things going on in the world. And then fast forward to 2004, I didn't really expect it to be a big story. Again, that was the next year that it conflicted. And all of a sudden, it's this big story, and they're talking about it on talk shows outside of sports. Is it okay to miss work for a religious holiday? I wasn't necessarily prepared for that. But looking back, it was a really good thing. And I'm happy that I didn't shy away from being different from the norm. Because even if you're different from the norm, there's a lot of people that are like you, and those people are proud to be able to say, hey, there's someone like me that's having success and is doing the right things. And that's the lesson that I felt was important for me to take out of it, but also to share with other people.

Adam: Shawn, what can anyone do to become more successful, personally and professionally?

Shawn: I think it's important to define what success is. For a lot of people nowadays, it's about how can I make more money? And that isn't always the best definition for success, right? An example is, my wife has a clothing store. And she loves it and does well and it's profitable, but it's not a type of situation where someone could necessarily have a great lifestyle living off of that amount of money. But for her, she loves what she does. It's important for the community. And she employs a lot of young girls in high school and college and mentors them. And so, that's the idea of success is to have something that is important to the community with GreenFly. I'm so proud that we have quite a few employees now that are passionate about it. People are growing their careers. And as a product, we're delivering a product that's helping leagues better and teams and different organizations better manage their content flows. And in this world today, that's successful. As we're helping organizations solve problems and finding success is the important thing. And my goal coming out was to build a successful tech company that I enjoyed the product and I enjoyed the opportunity. And so, right now, it is a success. Yeah, I would like to keep getting bigger and doing more things and solving new challenges, of course. But taking it one step at a time is pretty important.

Adam: Have a definition of success. Your definition can be different from my definition. I love your wife's definition of success. And regardless of what your definition of success is, focus on attaining it.

Shawn: I agree. It's all about having a goal. And that goal could change. The scale of the opportunity could be much bigger or smaller than you think. Our goals as a company have changed a ton, but underwriting success as continuing to grow as a company and a product and grow the opportunity.

Adam: Shawn, thank you for all the great advice and thank you for being a part of Thirty Minute Mentors. 

Shawn: Thanks, Adam. Thanks for having me.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

Follow Adam on Instagram and Twitter at @adammendler and listen and subscribe to Thirty Minute Mentors on your favorite podcasting app.